US4288606A - Esters of prostacyclin-type compounds - Google Patents
Esters of prostacyclin-type compounds Download PDFInfo
- Publication number
- US4288606A US4288606A US06/121,844 US12184480A US4288606A US 4288606 A US4288606 A US 4288606A US 12184480 A US12184480 A US 12184480A US 4288606 A US4288606 A US 4288606A
- Authority
- US
- United States
- Prior art keywords
- inclusive
- carbon atoms
- alkyl
- fluoro
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002148 esters Chemical class 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 title abstract 2
- -1 4-acetylphenyl ester Chemical class 0.000 claims abstract 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 abstract 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 229960001123 epoprostenol Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
- C07C405/0075—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system
- C07C405/0083—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system which is only ortho or peri condensed, e.g. carbacyclins
Definitions
- the present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,180,657, issued 25 Dec. 1979.
Abstract
Acyl-substituted phenyl esters of prostacyclin-type compounds, for example the 4-acetylphenyl ester of prostacyclin (PGI2) illustrated by the formula ##STR1## and including esters of the isomeric 6-hydroxy-PGI2 and 6-keto-PGF1α compounds, said esters having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
Description
The present application is a divisional application of Ser. No. 048,496, filed 14 June 1979; which in turn is a divisional application of Ser. No. 933,329, filed 14 Aug. 1978, now issued as U.S. Pat. No. 4,180,657, on 25 Dec. 1979.
The present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,180,657, issued 25 Dec. 1979.
Claims (1)
1. An acid ester of a 6a-carba prostacyclin analog of the formula ##STR2## wherein L1 is (1) --(CH2)n -- wherein n is one to 5, inclusive,
(2) --(CH2)p -- wherein p is 2, 3, or 4, or
(3) --(CH2)v --CH═CH-- wherein v is 1, 2, or 3,
wherein M3 is ##STR3## wherein Q is oxo, α-H:β-H, α-OH:β-R4, or α-R4 :β-OH, wherein R4 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R1 alkyl of one to 4 carbon atoms with the proviso that when R1 is tert-butyl the group ##STR4## is in the 4-position, wherein R3 is ##STR5## wherein R5 and R6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R5 and R6 is fluoro only when the other is hydrogen or fluoro; and the further proviso that neither R5 nor R6 is fluoro when Z is oxa (--O--);
wherein Z represents an oxa atom (--O--) or Cj H2j wherein Cj H2j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR5 R6 -- and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms; inclusive, fluoro, chloro, trifluoromethyl, or --OR7 -- wherein R7 is alkyl of one to 4 carbon atoms, inclusive and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different.
wherein R12 is ##STR6## wherein X is (1) trans--CH═CH--
(2) cis--CH═CH--
(3) --C.tbd.C-- or
(4) --CH2 CH2 --.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/121,844 US4288606A (en) | 1979-06-14 | 1980-02-15 | Esters of prostacyclin-type compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/048,496 US4236019A (en) | 1979-06-14 | 1979-06-14 | Esters of prostacyclin-type compounds |
| US06/121,844 US4288606A (en) | 1979-06-14 | 1980-02-15 | Esters of prostacyclin-type compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/048,496 Division US4236019A (en) | 1979-06-14 | 1979-06-14 | Esters of prostacyclin-type compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4288606A true US4288606A (en) | 1981-09-08 |
Family
ID=26726178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/121,844 Expired - Lifetime US4288606A (en) | 1979-06-14 | 1980-02-15 | Esters of prostacyclin-type compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4288606A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196617A1 (en) * | 1985-03-27 | 1986-10-08 | Syntex (U.S.A.) Inc. | [4.2.0]bicyclooctane derivatives, process for their preparation and pharmaceutical compositions containing same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2013601A (en) * | 1977-12-09 | 1979-08-15 | Haut Rhin Manufacture Machines | Process and apparatus for treating continuously moving articles |
-
1980
- 1980-02-15 US US06/121,844 patent/US4288606A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2013601A (en) * | 1977-12-09 | 1979-08-15 | Haut Rhin Manufacture Machines | Process and apparatus for treating continuously moving articles |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196617A1 (en) * | 1985-03-27 | 1986-10-08 | Syntex (U.S.A.) Inc. | [4.2.0]bicyclooctane derivatives, process for their preparation and pharmaceutical compositions containing same |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |